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John Cunningham has a robust background in sales and marketing within the insurance industry, with experience spanning over four decades. Currently serving as an Independent Field Rep at JMI Reports since November 2022 and Secretary of the Capital Improvement Planning Committee for the Town of Dudley, MA since July 2022, John previously spent over 22 years at Plymouth Rock Assurance Corporation, where responsibilities included establishing the Connecticut agency plant and enhancing relationships with independent insurance agents. Earlier roles include marketing positions at Trust Insurance, Norfolk & Dedham, and Commerce Insurance, demonstrating a consistent track record in agent appointment, territory management, and relationship building across multiple states. John's educational background includes studies at Northeastern University and Quinsigamond & Nichols College.